cheerleading tryouts
by m1tt
Summary: Miley and Lily try out for the last cheerleading spot. who will get it? the most talented or the one putting out
1. READ FIRST

I'm not responsible for your childhood death


	2. Try outs are fun

I am 28 years old and currently working as a gym teacher. I am an

all right looking guy. Just under 6 foot, brown hair and brown  
eyes. A little chunky but I was also pretty muscular due to all the  
sports I play. My involvement in sports was part of the reason I  
had gotten this job. This was my first year and by some weird turn  
of events I became the cheerleading coach. Two 14 year-old girls  
Miley and her best friend Lily were trying out for cheerleading. It  
was late Friday afternoon and we were the only ones in the gym.

There was only one spot left and they knew that they had to go all  
out to get it. I was the only judge and I was starting to have some  
trouble hiding my ever-present erection. They were both knockouts  
and the fact that i was twice their age did nothing to quench my  
thirst for some teen pussy. Miley had beautiful long thin legs and  
a relatively small chest. Her brown curly was very sweaty after the  
workout she had gone through and it just added to her attraction.

Lily had a slighty bigger rack with an incredible round ass. Her  
legs weren't as long or skinny as Miley's but i liked that she had  
more meat on her. Her blond hair was pulld back into a ponytail.  
They had both been pretty good but I had basically made up my mind  
that Miley was going to win this. Lily had made a few small errors  
when running her routine and her voice wasn't quite loud enough. I  
think they both knew the competition was already over. Lily looked  
pretty dejected and Miley was trying to console her. There was only  
one part left before they were done for the day. Technically I was  
supposed to go home and use the weekend to make my decision. But I  
was not expecting to think too hard about this decision. Although I  
knew I would be running this competition over and over again in my  
mind so I could release the tension I had built up recently.

The only part left was for one girl at a time to perform for me  
inside my office. I wanted to see how they could do with smaller  
spaces and this way I could focus on one at a time. The office was  
pretty incredible for a gym teacher's office. The room was huge and  
had a semiprivate bathroom. There was a female gym teacher that had  
an office just as big and was also linked to the bathroom. I knew I  
was doing pretty well at this school and I had to be careful to not  
blow it by revealing to the girls that they were turning me on. I was feeling pretty strained by watching their tryout for hours. I  
was planning on waiting until we were all done so I could  
masturbate in the luxury of my own home. Then I realized I would  
have to spend the next hour watching them perform their own  
routines which I knew would be even sexier then their earlier  
routines. There was no way I could wait another hour before I  
released. I knew that the girls would be focused on their routines  
and I could probably pop one off without their knowing. As I  
already said I knew I had to be careful because if I was caught my  
career was essentially over. Miley was first and she was looking  
unbelievable in this short skirt that barely made it to her thighs.

She was also wearing a tube top that was giving me a great view of  
her budding breasts. Can you now see why I decided to stop trying  
to accomplish the impossible task of keeping my erection down?

As she started her routing I unzipped my pants and started stroking  
my meat. I was doing my best to stay quiet but I am sure some  
noises came out. Miley didn't seem to notice however so I kept it  
up. Too damn soon the music stopped and Miley stopped dancing. I  
quickly stopped masturbating and cleared my throat.

"Great job Miley, you did incredible today. I will make my decision  
over the weekend and tell you my answer on Monday. I'll be here  
from 10-2 tomorrow if you have any questions.¨

"Thanks Mr. Fineberg, see you Monday.¨ I told her to send Lily in.  
As soon as Lily came in I remembered that Miley's cd was still in  
the stereo. I asked Lily if Miley was still out there.

"No Mr. Fineberg. I told her to go home and I would meet her at her  
house later.¨

I briefly wondered why Lily had sent Miley away but figured it  
wasn't important.

"Okay. Can you give her cd back to her then?¨

"Sure.¨

"So let's see this dance.¨

Lily put her cd in the stereo and started her routine. I unzipped  
again and resumed masturbating. Lily was wearing an even shorter  
skirt then Miley and a plain white t-shirt which had became  
transparent after sweating so much so I could see her plain white  
bra. Plus with that short skirt I kept seeing her thong panties and  
her tight round ass. I knew that I wouldn't last long with  
inspiration like this. However after only a minute Lily stopped  
dancing and turned off the stereo. I was a little pissed about  
being stopped when I was so close but figured as soon as I got home  
I could finish off.

"So did you cum yet?¨

I nearly fell out of my chair.

"What are you talking about?¨

"Oh come on, we saw your erection when me and Miley were dancing  
and I know I heard you jacking off under your desk.¨

All that was running through my head was that I was never going to  
work again. My entire career was flushed down the toilet after only  
a few years. When I came out of my funk I noticed Lily was kneeling  
in front of my chair.

"What are you doing?¨

"Making sure I win this competition.¨

Lily grabbed my dick which I never got around to putting back into  
my pants.

"Wow not bad, about 7-8 inches?¨

"8-9 actually.¨

"This will be a lot of fun then.¨

She lowered her head and started taking me into her mouth. I could  
feel her tongue working on my cock the entire time and it was  
incredible. It had just started and I already knew this would be  
the best blowjob of my life. Of course the fact that I had been  
watching two gorgeous teenage girls dancing for the last few hours  
would have made any release incredible. After only her third head  
bob she had my entire dick in her throat.

"God Im cumming!¨

That just made her head faster and I released right into her  
throat. She wasn't able to keep it all in her mouth and some leaked  
out onto her chin. After she swallowed the cum in her throat she  
used her finger to get cum on her chin into her mouth. The look on  
her face as she swallowed my cum was the sexiest thing I have ever  
seen. The look on her face was worthy of the final spot. But I knew  
I could do a lot more and if I gave up the chance to fuck this hot  
jailbait ass I would hate myself forever.

"Well I'm guessing that was not your first blowjob?¨

"No, it's the easiest way to get good grades. Much much easier then  
studying.¨

"Well thank you for the best blowjob of my life. With talent like  
that you must have a 4.0!¨

"No, I would but some teachers are girls, and I don't eat rug  
nearly as well as I give head. The female teachers usually only  
give me a B.¨

By now my dick which had started to soften was ready and raging for  
part 2. But I decided to wait just a little longer. I used all my  
willpower to keep my voice from cracking.

"So I know you give great head, but your dance moves still need  
some work.¨

"What, you mean I still don't get the spot?¨

"Not yet but I will give you another chance.¨

I turned on the stereo with a remote.

"Now lets see you dance one more time. But this time I want you  
naked at the end of the song.¨

She smiled her sexy slutty smile and got back onto her feet. As she  
started dancing I started stroking my cock again, this time in  
plain view of her. Lily's routine would have fit right in at a  
strip club. I couldn't help thinking she must have spent some time  
in a strip club at some point in her life. Maybe not as a dancer  
but she clearly had been studying up on how to dance. As she was  
bent down facing away from me she slid down her panties, giving me  
a great view of her incredible round ass. Lily continued dancing  
and the knowledge that she wasn't wearing any panties under her  
skirt was making me want to jump her right there. Somehow I managed  
to wait a little longer and enjoy her routine. Lily was massaging  
her tits through her shirt when she reached in, unsnapped her bra,  
and took it off through her right armhole. As I said her shirt was  
already basically transparent so I had a pretty clear view of her  
decent sized breasts. They weren't huge but they were still growing  
and it was obvious that she would have a decent rack on her at some  
point in the future. Finally the song was winding down and Lily  
quickly shed herself of her useless shirt and short skirt.

I looked her up and down in all her glory. She looked like a  
goddess. Her young body still glistening from the dance. Her  
breasts going up and down at a rapid rate due to her fast  
breathing. I had no idea that by end of the day I would be having  
sex with a girl this gorgeous. After a quick thank you to god, and  
a promise to go to church for the rest of my life, I told her to  
get herself ready.

Lily walked back to the desk and climbed up. She gave me a come  
here motion with her finger and when I got close enough she stuck  
her tongue in my mouth in a kiss that was more then I could have  
ever imagined. Then I reclined in my chair and watched an even  
better show then the strip dance. Lily first stuck her finger in  
her mouth and wetted it down. She then took her finger and slowly  
let it walk down her body. Her finger then went to the valley  
between her breasts and she started teasing me by putting her hands  
on her breasts and then quickly taking it away. Finally she took  
her wet finger and started circling her left nipple. Lily had her  
head thrown back in ecstasy as she continued to finger her nipple.

Her finger then continued its trek down her body between her legs.  
She continued her teasing methods and started circling all around  
her pussy. Lily finally started rubbing her clit with a slow  
deliberate motion. With the first touch she let out a moan that  
made my entire body jump with anxiety. Then she slipped a different  
finger into her pussy and started moaning even harder. I couldn't  
take it anymore and stood up and initiated a kiss even better then  
the last one. I then broke the kiss off and started nibbling on her  
ear. I sucked on her earlobe and lightly blew into her ear. Then I  
moved down and kissed her chin. Then I went down to her neck and  
sucked on it for a while. It didn't hit me til later that she would  
have to explain any hickies she got. Not that it would have stopped  
me but I might have left a few less hickies. I kept moving down and  
was soon at her bustline. I decided that with how much she teased  
me I definitely needed to get some revenge. I lightly blew on her  
right nipple. I gave it a test lick and started licking and sucking  
on it. Lily was still fingering herself throughout this so I  
grabbed her hand and pulled it away from her hot center. With my  
other hand I flicked her forgotten nipple. Her nipples were somehow  
harder then my dick at this point. If I couldn't feel them then I  
wouldn't think it was possible. I knew that I was affecting her a  
lot by now. She was so close to an orgasm that she was starting to  
shake. Then I moved away from her with a huge smile on my  
face.

"WHAT ARE YOU DOING! GET ME OFF! I AM SO CLOSE!¨

With all the pleasure she had already brought me I knew I had to  
stop teasing and give her the orgasm of her lifetime. I brought my  
head down and examined her pussy. She was definitely a natural  
blond. She didn't shave her pubic hair but there wasn't too much  
there because she was still so young. I lowered my head down to her  
hot creamy center and gave her pussy a tentative lick. It was the  
best thing I have ever tasted. Correction, this was the best thing  
I had ever experienced. I don't think anyone could have ever  
experienced something this good. I couldn't help myself and just  
dove into her pussy and started eating her out like I had never  
eaten someone out before. At the same time I used my nose to rub  
her clit and brought both hands up to massage her breasts. I took a  
short break from eating her out to look at Lily's face. I thought  
the look on her face after blowing me off was sexy but the look on  
her face was like comparing a piece of dog shit and filet mignon. I  
knew that I would never forget that look for the rest of my life.

"OH GOD I AM CLOSE! I AM GOING TO CUM HARDER THEN I HAVE EVER CUM  
BEFORE! KEEP IT UP!¨

With that motivation I buried my head back into the best place on  
Earth. Disneyland be damned. After winning the Super bowl the  
players should go here. It would definitely inspire the players  
even more. I was listening to her moans and I knew right when she  
was ready to climax. There was something that all of my former  
girlfriends loved that I decided to try. I took my tongue out of  
her cunt and licked my way down her ass crack and got to her anus.  
I licked around the anus and finally plunged my tongue in. It is a  
weird taste that I don't really enjoy but it is a guaranteed orgasm  
so I continue to do it every time I go down on a girl. With that  
final push Lily climaxed harder then I had ever seen a girl climax.  
I was glad the school was empty because with the scream she let off  
could be heard throughout the building. And to think i thought her  
cheers weren't loud enough! I laid back into the chair. With how  
much effort I put into it it seemed like I had already ejaculated.  
I had almost forgotten all about my erection when Lily grabbed it  
with her right hand. I was ready to finally give this girl fucking  
of a lifetime. I stood up and got on the desk mounting her. I was  
about to penetrate her when I remembered I didn't have a condom.  
Lily saw my hesitation.

"Don't worry; I am on the pill.¨ With nothing holding me back I was ready to finally penetrate her. I inched my dick into the tightest pussy I had ever felt. With all of her experience I couldn't believe she was this tight. I was starting to think me and Lily had some kind of connection. Once again she seemed to know exactly what I was thinking.

"I said I gave all my teachers head to get good grades. I've only  
had sex like 2-3 times. And you are the biggest dick i have ever  
had in my pussy.¨

I must admit that made me feel much better, especially  
about being the biggest one to penetrate her. So with nothing  
holding me back I once again was ready for the best sex ever. I  
lifted her right leg up to my shoulder and started thrusting. I  
could only get 4 inches into her. I decided to give her some time  
to adjust to my dick in her cunt. Eventually she used her hands to  
lift herself up and thrust her body towards me. With that my entire  
8 inches were buried in her. I knew I would have to be careful or I  
would be spent in less then a minute. With one hand I started  
massaging her left breast and my other hand I started toying with  
her clit. She was thrusting back at me as hard as she could and  
gasping in a way that was more adorable then anything else in my  
life thus far. I remembered her reaction to me tonguing her asshole  
so I figured maybe she had an anal fetish. I took my hand off her  
breast and caressed her skin all the way to her ass. I hadn't taken  
the time to touch her ass so this was my first experience feeling  
it. It was much better then I had expected and I had to spend some  
time squeezing her luscious behind. I thought her breasts were  
exquisite but her ass was nothing less then a masterpiece. I could  
grope this ass for hours and never get tired of it. Unfortunately I  
realized that I was much closer to cumming then her so I had better  
get to work on her. I didn't want to leave her so close to an  
orgasm so I had to really step it up. I started placing one finger  
into her asshole. I thought her pussy was tight but her rectum was  
like a vice. I knew that I had to find a way to put my dick there  
somehow. There was no way I could do it today but at some point in  
time i knew i would fuck this ass. I was having trouble getting  
momentum now so I took my dick out and put her on her knees and  
entered her doggy-style. I shoved my thumb into her asshole and she  
screamed in orgasmic bliss as she came again. The feeling of her  
walls closing in on my dick was too much and with my last bit of  
will power I withdrew my dick and coated her tits with my cum.

I then leaned back and fell of the desk. I landed hard on my back  
but I was still the happiest man in the world. Now I just have to  
find some way to make this a repeat occurrence.  
"Well you definitely earned that spot.¨  
"You know that we can't do this again right? If I get caught having  
sex to get something from a teacher then my entire system is  
ruined.¨

"Okay, well I hope you remember that in a few months I have to  
decide who will be the next cheerleading captain. If you want that  
spot then you will need to repeat this.¨  
"Well we'll see. For now I am happy just having a spot on the  
squad.¨

Lily cleaned up in my semi-private bathroom and put her clothes  
back on. When she was walking out the door I remembered the  
cds.

"Don't forget your's and miley's cds.¨

"Okay thanks.¨

All of a sudden I remembered something else, something that scared  
the shit out of me.

"Hey are you going to tell Miley about what we did here today?¨

"Of course not, she has no idea about my plan for good grades. She  
still thinks I am a virgin! Her plan is for us both to lose our  
virginity together during senior prom!¨That brought an image into my head.

"Together? Do you think I can watch? Or possibly join in?¨

"Haha, believe me if you could convince her to have sex with me I  
would let you do whatever you want to my body.¨ My mission was clear, I had to convince Miley to not only have sex before prom, but to have sex with Lily and me. I knew it would be hard but the reward would be so worth it.


	3. Miley try's out

Lily was feeling pretty good about herself about making the team. The fact that she had a few orgasms was adding to that a little bit. So after the tryout and a quick shower she went to pick up Miley before heading out to the mall. Miley did not know what Lily had done so she was pretty confident she would be given the last spot. They were best friends and Miley thought Lily could use some cheering up "Don't feel bad Lil. You did your best. Maybe he liked your routine better anyway." Lily decided to explain why cheerleading meant so much to her, just in case Miley found out how she "earned" the spot. "Well I guess we won't know who did the best until Monday. I really need the spot though. My family has a history with cheerleading. Every living female relative was on the cheerleading squad and only one was not the captain. Mom has been putting a lot of pressure on me to make it." Lily also figured this would prevent Miley from being sad when Lily won. "Wow, I didn't know that. Now I think I would rather you got the spot then me." Miley thought "Shit! There is no way he will choose Lily. She made so many mistakes during her routine. Unless she dazzled him in the final competition when I wasn't there she is sunk." After a few hours of shopping and general gossip the girls parted and went home. All Miley could think about when she was lying in bed was the look on Lily's face when she found out Miley had won the last spot. Miley decided to go to the school tomorrow and talk to Mr. Fineberg. He had mentioned being there if she had any questions.

The Next Day…

'Hi Mr. Fineberg." "Miley? What are you doing here?" With one look at her face I realized I would have to take away the spot she rightfully earned and give it to her best friend because I had sex with her. I felt like shit. "I need to talk to you about that cheerleading spot" Miley said bringing me out of my own thoughts. "What about it? You know I won't be making my final decision until Monday. And I can't tell you in advance who will get the spot." "I know sir. But I decided to back out. Lily wants this much more then I do. She should be on the squad instead of me." To say I was floored would be an understatement. I could now give Lily the spot and not feel guilty at all, aside from the fact that I slept with a minor half my age. But I sensed something from Miley and decided to toy with her a little bit.

"Well I wish I could help you. But you signed a contract saying you were trying out and that you would stick with it." "Can't you let me slide on that?" "Well I could, but if I make an exception for you and break a contract the school would have grounds to fire me. And since this is only my first year I don't have the clout needed to preserve my job." Miley looked pretty dejected at that. "Well what if there was a way I could convince you to give Lily the spot?" This was sounding pretty interesting but I played dumb. "What could you do? I have already seen how talented you are and I have compared it to how talented Lily is. It seems like my choice is clear."

Miley walked up close to me and whispered in my ear, "what if I convinced you with something other then my dancing skills?" Well by now I was very erect and pretty sure we were on the same page. "What are you going to convince me with?" "Oh you'll see" she said with a smirk. That was when I felt her hands on my chest. She started unbuttoning my shirt and kissing my neck. I tried comparing Lily's and Miley's kissing and Miley was definitely more timid. Lily had admitted to having sex before and said Miley was a virgin. I was having a little trouble believing it now though. "Oh Miley, what are you doing?" "Just using what God gave me to help a friend out. With my shirt completely unbuttoned Miley tried taking it off but I had to help her a little. Now I could see how nervous she truly was. There was no way she had as much experience as Lily. "Before we do anything I need to know how many you have done this to before me." "Well actually I am a virgin. I was going to have sex with this boy Jake. He had already stripped me naked and gotten me ready. But when I touched his dick through his pants he came. Then he moved away and I haven't found anyone else I want to have sex with." Then she leaned right next to my ear, "Until now." I swear I was way too close to cumming in my pants after that. I knew I needed to stall her a bit so I could regain some control. "Are you sure you want me to be your first then? I don't want to make you do something you will regret later." "Oh don't worry. Me and Lily both have the hots for you. We were checking you out the entire time we were trying out yesterday. And I know we affected you. We could see your erection all day long. What did you do with that hard-on? I thought I heard you jacking off during my personal dance routine. It made me so hot. Did you get off then or wait until Lily's routine?" Damn I was not as sly as I had hoped. But on the other hand because of it I had already fucked Lily, and unless this was a dream I was about to take Miley's virginity. "Oh I came during Lily's routine. And with the tension I gathered up watching your two fine asses all day it was quite an ejaculation." "Oh God you don't know how hot that makes me. It makes me want to touch myself." "Why do that when you have me here?"

With that I quickly stripped her shirt and skirt off of her teenage body and gave her a quick once-over. Damn was she fine! Two of the finest teenage girls I had ever seen were naked in my office in the last two days. I love this school! When I looked her over I noticed something that I couldn't believe I had missed. She was not wearing any underwear! "Dirty girl. You knew what we were going to do all along, didn't you?" "Well I figured either I would have to convince you to give Lily the spot, or I would reward you for giving Lily the spot. Either way I knew we would be fucking and this would make you hot." She was definitely right about that. To think that she was walking around in a short skirt and no panties made me hornier then I had been in a very long time.

I grabbed her neck with both hands and leaned in for a kiss. While she definitely had less experience then Lily it was better in some ways. I got to be the dominant one this time. Yesterday Lily was the one really in charge. It was exciting knowing that I had lost control but at the same time I had never been the submissive one before. Kissing Miley felt a lot more normal. Leaving one hand on her neck I used the other one to explore her body. She was definitely a couple cup sizes below Lily in the breast department. But they felt so perfect for her body. Any bigger or smaller and she would have looked unnatural. After tweaking her nipples a bit and feeling her moan a bit into my mouth I let my hand continue its trek down her body. Finally I stopped kissing her lips and kissed her entire face. I kissed each individual lip and her nose. I sucked on her earlobe. Then I brought my mouth down to her neck. I moved the hand on her neck down to her ass. I learned my lesson with Lily. Grab the ass early. I did not spend as much time with Lily's ass as I would have liked. I gave Miley's neck short hard kisses.

Meanwhile my hand finally reached its destination between Miley's legs. I really wanted to tease her, so I brought one finger to her inner folds. Damn I couldn't believe how wet she was. She was more turned on by this then I thought. Not even Lily was this wet. "Oh God that feels so good. I can't wait to feel your dick in me." Well she really knows how to get a guys attention. After slipping my finger up the knuckle into her I withdrew. I could hear her whimpering. I moved my mouth down to her breasts to increase the torture. "Please keep fingering me. I need to release!" I knew that if I continued to tease her it would make her eventual climax even better so I didn't give in. I brought my lips away from the valley in-between her breasts to say, "Remember patience is a virtue. This will just make your climax feel even better." "You are evil! Just get me off! I am burning up!" That brought a huge smile to my lips. I couldn't wait to sink my dick into her. But I knew it would have to wait so kept up the teasing. I put my finger back into her pussy and let another finger nuzzle her clit. "Oh God! Keep it up!" I knew I had to be careful or she would be brought to orgasm a lot sooner then I wanted but I loved hearing her moan. I finally let my mouth clasp her nipple. Miley's moaning was really getting loud now. I took my hand away from her ass and squeezed her other tit. I knew that with how tight Miley was I would have a hard time squeezing my dick into her. I couldn't even fit my other finger in. I was pumping it slowly in and out of her pussy but I couldn't get much more in. "Relax Miley, I won't be able to fuck you if you stay this tense. My dick won't fit inside you." "Okay I'll try." After a few more pumps I knew she needed some oral action. I reluctantly took my mouth away from her nipple and started kissing my way down her body again. I took my finger out of her cunt which clearly pissed Miley off. "WHAT ARE YOU FUCKING DOING! I AM SO CLOSE. DON'T STOP!"

With that I brought my tongue down and teased her clit. "OOH OOH YES! PLEASE KEEP GOING!" Then I put my tongue back into my mouth and scraped her clit with my teeth. Miley was panting now and I knew it was only a matter of seconds til she hit sweet release. I finally brought my tongue down to her pussy and entered her. "YES YES YES OH GOD YESSS!" I took that as a good sign. I used my nose to hit her clit and my mouth was flooded with her cum. With that her knees collapsed and she fell to the floor. "That was the best orgasm of my life! You are a GOD!" Well that keeps my self-esteem really high. Unfortunately my dick was burning a hole through my pants. Somehow I was still fully dressed from the waist down. I unzipped my pants and took them the rest of the way off. My dick was pointing straight out with the material of my boxers barely holding it in. "Oh wow! That is what you are packing. I was expecting something much smaller." Well that hurt a lot. "Are you saying you don't want to continue?" All that was running through my head was please god no, have a heart! "I didn't say that. But I am going to have to lube you up." Jackpot! I lowered my boxers off my painfully erect dick and sat back into my chair.

Miley got up onto her knees and looked at my dick for a while. Finally I had to ask her if there was something wrong. "Well this is the first time I have seen a real dick. I just can't believe how big it is." Again my ego was feeling pretty good but I needed to release quickly. Finally Miley brought her hand up and gave it a few quick pumps. I couldn't help groaning. Miley seemed to like that and brought her head down to my dick. She opened her mouth and gave my dick a tentative lick. "Well that is better then I expected. A little salty but not at all bad." She lowered her head and took the tip into her mouth. I sighed at the warm feeling her mouth gave off. I knew her pussy would feel even better and that thought almost made me shoot off right there. With one hand on the bottom of my shaft she brought the other hand up and started playing with my balls. She kept massaging and kneading them. I knew I would bust soon. She kept lowering her head down on my dick but she was definitely lacking in experience. She couldn't get a good rhythm and she scraped her teeth hard on it a few times. Eventually I had to stop her.

"Was it really that bad?" "No of course not. I just want to move on so we can both be pleasured." No reason to hurt the girl's feelings. She was clearly doing her best. But she clearly needed practice. I would of course be willing to be her practice dummy but that would have to be another time. Her cunt was calling for me. I was ready. In case Lily wanted another go I had grabbed some condoms yesterday and put them in my wallet. I dug one out and put it on. "So Miley, how do you want to do this?" "Any way is good for me. I just want to feel your dick in my vagina." I decided to let her dictate the pace then. I knew that with how tight she is I would have trouble holding back from hurting her. "Okay, I will stay in my chair and you will mount me. Sound good?" "Great!"

She got on her knees on top of me and let her legs go to either side of me. I positioned her right above my cock. "Now you will have to do most of the work. Okay?" She nodded and lowered herself until my dick was entering her. It had been so long since I had sex with a virgin. The only virgin I had sex with was the one I lost my virginity to. That was at least 10 years ago. I had no idea what to expect from her. Miley was biting her lip because she was so nervous. I bent her down and kissed her. "Relax. You are in control. If you stay tense then you won't enjoy it." That seemed to calm her down. She finally let gravity start its work. She lowered onto my dick and the first 2 inches went in. OH MY GOD! She is tight! Miley let out a pained moan. "Don't worry. Take your time. Get used to it before you go any farther. It will feel a lot better." "Thanks Mr. Fineberg. I am glad I am doing this with you." With that I moved both of my hands to her sweet derrière. I gave it a big squeeze which had the unexpected effect of making her drop down onto my dick. Now four inches were in and I could feel her hymen.

"This will be the hardest part. After this the rest will be easy." Not exactly true but I had to say something. Plus maybe it is true. It's not like I ever had a hymen break. With tears in her eyes she dropped down hard and let my dick break on through her hymen. "Oh my god this hurts!" Don't think about it. Think about how good it felt when I was eating you out. Once you get used to my dick in you it will feel even better then that. She trusted me and waited. After 2-3 minutes she raised her body up and slowly lowered it back down and went back up. My dick felt on fire. I knew I would cum soon and I wanted her to cum with me. I took one hand away from her ass and started playing with her clit. "Oh Wow! That feels incredible!" With my other hand I started playing around with her asshole. Not entering it but just toying with hit. Letting my nail nudge its way in a little bit. She had forgotten all about the pain of my dick in her. She dropped all the way down hard onto my dick and my entire dick sank in. I was expecting her to scream in pain but apparently the pleasure had kicked in. Miley started bouncing up and down on my dick slowly. Her mouth open in frozen screams. I bent my head down and captured a nipple in my mouth and lightly bit down on it. At the same time I finally thrust my finger into her asshole and thrusted my body upward hard. My dick entered her fast and she gave out a scream. All the added stimulus was too much for her and she had a huge orgasm which set me off as well. I didn't even have enough time to pull her off my dick. I just shot right into the condom. With that we both fell asleep, my dick still buried in her.

About two hours later I woke up. "Figures I was dreaming. What a dream though." My dick felt incredible but there as some kind of added weight on me. I opened my eyes and saw a girl resting on my chest. I realized it actually happened. I took the cherry of one of the finest girls at this school. I gently shook her awake. "Miley, wake up." "Huh? What's going on? Oh Mr. Fineberg! I hope this convinced you to give Lily the spot." "I can tell you without a doubt that Lily will be the recipient of that spot. But this was a long way to go just to give your friend a spot. You'd think if you were going to fuck someone just for a spot that it would be for you?" "Well Lily is my best friend. And she would do the same for me." I knew differently but didn't feel like telling her that. "So you think Lily would be willing to sleep with someone for a spot?" "Definitely. We had a plan to lose our virginities at our prom. But she lost hers a long time ago. It kind of makes me jealous." I saw my window. "Jealous huh? So do you have sexual feelings for Lily?" "Well I have had dreams about her before. In fact if I were to have sex with a woman it would definitely be Lily." Interesting. I remembered Lily telling me that if I could convince Miley to have sex with her I would be able to do whatever I wanted to Lily. Now that I knew Miley was interested I knew I would find a way to make this happen.

"Mr. Fineberg? Are you okay?" "Yeah I am fine. I guess you should be heading off. You can clean up in my bathroom. And remember that I choose cheerleading captain in a few months. If you want Lily to be the captain you will probably have to help with the decision making process." "I will definitely do that. Thanks for the best experience of my life. Bye." Now I could focus on how to get those two together for some wild fun. Plus how I convince them both to fuck me again. A plan was forming in my mind but it was pretty risky. Oh well, there was no way I could stop now. I had already put my career on the line by fucking underage girls. Why not try for more?


	4. More fun

After fucking both Lily and Miley I knew I needed some more young pussy. They had both told me that it was a one-time thing and we had to stop. There was no way I could live with that so I came up with a plan. I talked to a girl that I knew was an incredible cheerleader but who had decided not to tryout. "Please try out Katie. I am in a bind here. I don't know which one is better and I am supposed to make my decision today. This way I can see them again and I can also get someone else's opinion." "I don't know sir, are you sure you just can't ask them to try out again?" "If I admit I can't choose between the two of them then the principal may decide I don't deserve to be Cheerleading Coach. I will pay you 10 bucks to tryout with them." "Make it twenty and you got a deal." "Fine, but you have to go all out during the tryout, that way they won't suspect anything."

With the deal in place I went to talk to Miley and Lily. "I am sorry girls. The principal has ordered me to hold tryouts again. Katie has decided to tryout. She was part of the all-state cheerleading team last year and we can't afford to pass her over without seeing her tryout." "But sir! We already went through tryouts! Can't you just see her compete and judge who is better?" asked Miley. "Well I could. But the principal said I have to make sure to pick the best one, which means I need to see how you 3 compare. The only way to do that is for all of you to perform at the same time." Now that I had set everything up I was ready to enjoy those teen pussies once again.

Friday, the day of tryouts

Once again I watched the girls perform and my erection was straining inside my pants. This time there was the added bonus of watching Katie perform. I wished I could screw her to but settling for Miley and Lily was fine by me. Lily was doing a lot better this time. That's very good because when I give her the spot I knew some people would question my decision if she was horrible. Eventually we got to the individual performances. Miley was first. "Lily already has the spot right? There is no need for us to fuck again?" "I dunno about that. You saw how incredible Katie was out there. I can't pass her up because of one fuck." "You planned this all along didn't you?" "What do you mean? I didn't know Katie would be good. I swear if Katie was horrible then I would give Lily the spot even if you didn't fuck me." "Liar. Oh well, at least I get another incredible lay out of this deal."

Miley quickly stripped down and walked over to me. She gave me an aggressive kiss; she was biting my lip like she wanted to suck the blood out of it. And her hands were busy too. One was unbuttoning my shirt while the other reached inside my pants to grasp my hard-on. I put one of my hands in her silky hair and grabbed her naked ass in the other. My main point to this scheme was not to just fuck them, but to butt-fuck them. I remembered how tight their assholes were. There was no way either of them had had anything inside their assholes before. I couldn't wait to be the first. After a few seconds of fondling Miley pulled away with her eyes wide. "Your dick! It feels so much bigger! It's huge!" In preparation for this day I had been taking dick enhancer pills all week. It made me longer, thicker, and it made me last much longer. I was prepared to give these girls of the fucking of a lifetime. "I was feeling sick last week. I couldn't get fully erect." Miley quickly unzipped my pants and pulled them and my boxers to my ankles. "HOLY SHIT!" It was pretty obvious why she was surprised. Thanks to the pills my dick was 12 inches long and 3 inches thick. I was basically a dick with legs.

"It doesn't scare you, does it?" "No, it makes me horny. I want that monster inside of me." With that Miley jumped on my lap and started making out with me. I used my hands to get her ready for the fucking to come. I brought one hand down to her fuzz-covered muff and started tapping on her clit. Her moans were vibrating inside my mouth, along with her tongue. With my other hand I started rubbing all over her ass, only stopping every once in a while to stick my fingernail inside of her asshole. Every time I did she would let out a cute little EEP sound and then continue on with the make out. Eventually I got tired of making out with her and picked her up off my lap. Then I stood up and put her in my chair.

Earlier in the week I had realized the chair elevated someone into just the right position for muff-diving. I had been looking forward to trying this out all week. I lowered my head and inhaled her scent. Then I noticed her pubic hair. She had shaved it into a cute pattern resembling a butterfly. "Well looks like I'm not the only one who expected this to lead to sex?" Miley blushed. "I was ready in the off chance that this happened. Don't think I was just going to throw myself at you." With that I knew what I had to do; I had to make her beg for it. I had to make her plead with me until I was nice enough to give her the orgasm she desperately needs. I leaned in and kissed her bellybutton, diving my tongue inside over and over again. Then I let my tongue crawl its way down her body slowly. Right when I reached her molten core I turned away and started licking down her leg. I went down and back up, making sure to nip at her skin every once in a while. Then I got back to her muff and started flicking her clit with my tongue. Miley let out the most sensual moan which quickly turned into a groan as I left her clit and started licking down her other leg. I repeated my previous actions a few times. Miley was visually shaking now as she was ready for me.

"You can stop this anytime. Just tell me what you want." "You know what I want!" "A new bike? A purse?" "TO CUM! MAKE ME CUM! I WANT YOU TO EAT ME OUT AND THEN FUCK ME LIKE THE WHORE I AM! IS THAT WHAT YOU WANTED TO HEAR?" "Precisely." With that I finally took her clit inside my mouth and sucked on it. I gently bit down on it and her gasps were making my dick throb harder then ever before. With that I took her clit out of my mouth and put my tongue inside of Miley's dripping cunt. I knew that with how I had teased her and the moans she was making that Miley was only a few seconds away from a huge climax. I raised one hand and pinched her right nipple extremely hard and that brought her climax. I was glad I remembered to turn the music on as loud as possible or Lily and Katie would have heard her screaming easily.

When Miley came down from her orgasm she was looking at me with glazed over eyes. "Wow! That was…WOW! So I guess it is your turn?" I stood up and went over to my new couch. It was a fold-out couch which I had bought earlier in the week in preparation for this event. The school board said I could have it in my office but I had to pay for it myself. I knew that just this one fuck would make the price worth it. After getting the bed ready I sat down and patted down on it, trying to get Miley to come over. Miley sauntered over with a sexy smile on her face "Thought you said you weren't expecting this to happen?" "Who said this bed is for you? I have a lot of late nights. Sometimes it is just smarter to stay here for the night so I am already at school in the morning." A huge lie. I'm a gym teacher and a cheerleading coach. Why would I need to stay late? But the school board bought it and Miley seemed to accept it.

"So how do you want to do this?" "Well even with how wet you are I don't think you are ready to take me inside of you yet. Maybe you should try lubing me up?" "Works for me." Her glazed eyes had turned into lust filled dagger. Miley leaned in and started kissing my neck. Then she lowered herself and started toying with my nipples. It felt weird but so good. Miley seemed to be enjoying the taste of my body a little too much. Miley started exploring my body with her tongue and eventually got to my throbbing cock. She hesitated for a second and then licked all around it. Miley put my balls into her mouth and alternated which one she would suck on. She grabbed my erect dick and started pumping it up and down. My precum was starting to collect at the top and when Miley saw this she took my nuts out of her mouth and lowered her head onto my dick. She licked the precum off and then pulled back. "MMM this is tasty stuff. You should bottle it." With that she lowered her head back down and started bobbing. Last time she blew me she was clearly inexperienced and it did nothing to get me off. This time however she quickly got 8 inches down her throat and kept going. "OH MY GOD! MILEY YOU ARE INFUCKINGCREDIBLE! YOUR MOUTH IS LIKE A VACUMN!" Within seconds my entire dick was in her throat and it was the sexiest thing I had ever seen. This girl, who only 1 week ago lost her virginity to me, is sitting on the bed with my foot-long cock in her throat and her eyes looking at me like she still wanted more. The look on her eyes was too much for me and I shot my load unexpectedly down her throat. I didn't even have time to give her a warning. Miley took the dick out of her mouth as quickly as she could and let the rest explode all over her face. She scooped a lot of it up but eventually she just grabbed a towel and wiped the rest of her face off. I couldn't believe the amount of cum I shot. Those pills must have an added effect of increasing the amount of semen my body produces.

"Can I get a warning next time! I loved the taste but I almost choked on that load!' "Sorry, I couldn't help myself. You are the sexiest thing I have ever seen." I lowered my head and kissed her. The cum disgusted me a little but I knew it was what she wanted. Plus she had already wiped everything off so there was not much left to taste.

"So are you ready for another round?" "Yeah but we better hurry. We have already been in here for a long time." Then I pushed her onto her back and mounted her. I brought my dick right to her tight opening and looked at Miley. She had her eyes closed and seemed scared of what was coming. I kissed her again and whispered in my ear. "Don't worry, I won't just bury this in you. I want you to enjoy this too." "Then shut up and make me squeal like a pig." I smiled and shoved my dick into her, burying about 4 inches in before I met too much resistance. "Ahhh! So thick! Okay, Okay, FUCK ME!" I started thrusting back and forth. I was really surprised. With how much her blowjob technique had improved in a week I figured she must have been having a lot of sex. But her pussy felt just as tight as I left. I made a note to ask her about that later. The hungry look on her face persuaded me to keep going. I couldn't take my eyes off her. She was beautiful. That was when I realized I may be falling in love with her and Lily. That scared the shit out of me but I pushed that thought out of my mind and continued fucking her.

Miley wrapped her lithe legs around me and started pulling me in harder. I figured if that was how she wanted it, that was how I was going to give it to her. I pulled all the way out of her and ignored her whimpering. Then I pushed into her with all of my strength. She let out a huge breath and I think I knocked the wind out of her. I let her regroup a little and then pulled back and thrust just as hard. Miley thrust back at me and this time my entire foot-long monster sized dick impaled her. I had to stop and reflect on how much I love my life. Who would have thought that being named the cheerleading coach would be the best thing in my life?

Miley was wondering why I stopped and she used her legs to pull me in and let me know she was not done yet. Then I started fucking her in earnest. I gave her everything I had. By now I had forgotten all about Lily and my plan to fuck her later. I was going to fuck her until we were both unable to stand. I started massaging her breasts with both hands, bringing them together and then I lowered my head and started licking all around them. The sounds she was making was making me near climax way too soon. I knew I had another round left in my dick but I was not sure if my body would be able to go through with it. Miley's screaming brought me back to earth and I watched her face contort into a look of pure ecstasy. Her walls closed in around my dick and made me come to the brink of climax but I fought it off. I wanted to do one more thing before I ejaculated.

I pulled out and climbed off of her. "You were even better then last time! But you didn't cum, did you?" "There is something I want to try first. It may hurt a little at first but it will become the most pleasurable thing you have ever felt." Miley's eyes went wide. "You don't mean…anal?" "Yep, don't worry, I have plenty of lube and I will go as slow as you want." "Okay, but be careful." I got up and went to my desk and grabbed the tube of lube I put there earlier. I spread some all around my dick and then walked back to the bed. I turned her over onto her knees. I put lube on one finger and plunged it into her rectum. I knew Miley was hurting but she kept quiet. That made me love her even more. After a while I was able to get two lube-covered fingers into her asshole and I thrust them in and out rhythmically.

I knew she was ready when she started thrusting back at me so I withdrew my fingers. Miley gasped at the feeling of emptiness inside her. "Stick it in, please stick it in." I mounted her and put my dick back into her pussy just to get some more juices onto my cock. I brought my dick up to her asshole and slowly pushed it into the tightest thing I had ever felt. She was like a vice. I almost shot my load inside of her right then. I took a few seconds to catch myself and then I started thrusting. I could get only a few inches inside her no matter how hard I tried. There was no way I would get it all inside her before I cummed but I didn't care. If the sounds Miley was making were any indication she didn't care either. She was clearly in pain but she was also having more pleasure then every other orgasm combined. I brought one hand down and started thrusting four fingers into her cunt and with my thumb I brushed her clit. That did it and Miley was orgasming again harder then I had ever seen someone cum. The way her body was flopping around made my dick explode deep inside her asshole. I pulled out and let the rest cum all over her back and ass.

Then I fell back and collapsed on the bed. "Wow, well my mind is made up." "Oh shit! Look at us. Lily and Katie will know what we have been doing." "I have a shower in the bathroom. Let's take a quick shower and then you can go." "Us taking a shower huh? I think we would even dirtier." Miley said in a suggestive tone. I leaned over and kissed her one more time. "Well whatever happens, happens." Miley giggled and followed me into the bathroom. Somehow I still had enough energy for one more round. When we got into the shower I picked her up and wrapped her legs around me. I pushed her up against the wall and started thrusting while making out with her more passionately then I had ever kissed a girl before. We both were brought to quick orgasms and then cleaned each other up.

"I almost forgot, how did you get so good at blowjobs in just a week?" "Well I practiced on vegetables. I thought we may do this again so I decided to get ready in advance. Did it work?" "You were incredible. I can't wait to feel those lips around my dick again." 'Easy, big guy. Who said I would do this again?" "Oh I know you want my dick inside you one more time. Plus you haven't felt my dick shoved all the way into her asshole." "Well that is not entirely false. I'll see you in a few months when Lily is going for cheerleading captain." With that Miley left and I was alone in my office again. Not for long though as Lily came in only a few seconds later. "So are you ready for another round of hardcore fucking." Oh shit I forgot all about Lily. Guess I have to bite the bullet and give her a good old-fashioned fucking. Unlucky me!


	5. Lily is a bad girl

As soon as Lily walked in I knew I was going to have a hard time fucking her again. After the incredible sex with Miley I was feeling exhausted and knew I had at best one time left in me.

"Is there something you want me to do first, or do you want to get straight to the fucking?"

"Well why don't you tell me what you want to do? And be graphic."

I was hoping whatever she said would be enough to get my erection back. I wanted to be ready for her when I took my clothes off because I wanted to see the look on her face when she saw how much my dick had grown.

"Hmm, okay. I want you to strip me of these tight restraining clothes. Then I want you to lick all over my young body, finishing by giving my young tight cunt a long thorough tongue-fucking until my body gives out in orgasmic delight. Then I want to feel your big hard cock in me, pounding harder and harder until you spill your seed straight into my tight inexperienced cavern."

My plan worked and my dick was brought back to full attention and making a huge dent in my pants. I thought briefly about turning the couch back into a bed but I was fairly certain me and Miley had left some evidence of our love-making there. As it turns out I later found her panties left there. I guess she wanted to leave me a memento. Nice of her but it could have ruined my plan.

"Well then come over here and let's get started on your list. What was first again? Oh yes, now I remember."

I almost tore through her shirt getting it off her body. It had buttons but I was feeling to horny to bother with them. Luckily only half of them snapped off so she would be fine getting home. If not looking a little odd. I started kissing her body with every button that became undone. I was now really glad I had drank all of those bottles waters because otherwise my lips would have became chapped pretty quickly. I quickly discovered she had forgone the bra this time. I have no idea how I didn't notice this during her routine. Guess I have to get my eyes checked. I then brought my mouth back to her young nubile tits and proceeded to suckle them like a newborn. If I had learned one thing about my latest endeavors it is that there is no taste like a teenage girl. No matter where I put my mouth I end up craving more of this heavenly taste and it is always nearly impossible for me to drag my mouth away.

"You're…OH GOD…skipping step one. You're supposed to…UHHH…strip me completely before you taste me."

"Does that mean you want me to stop? Or maybe I just let you go now? I could give you the spot on the squad now. If that's what you want. Tell me what you want."

With that I gave her nipple a sharp bite.

"UHHHH…NEVERMIND…DO WHATEVER YOU WANT. JUST PLEASE DON'T SEND ME OUT OF HERE WITHOUT FUCKING ME!"

Good good. I may be able to get her to come back for more, even after she makes the squad. Just got to make sure she craves me more after this. After this incredible week I don't want to go back to just masturbating to these teenage girls and their gravity-defying bodies. I want to continue fucking them until I can't even remember how to masturbate.

Satisfied that I was once again in control of the situation I brought my attention back to the lovely pair of breasts in front of me. Licking them, sucking them, biting them. A couple of times I brought a hand towards her neglected breast and pinched it right as I bit her other nipple. The sound she made was so primal, so guttural that I knew I had her right where I wanted her. She was mine. Every once in a while I swiftly switched which breast I was toying with. The sounds she was making caused my dick to jump so many times I don't know how my jeans stayed intact. After lavishing them with my tongue for several minutes I finally started kissing my way back down her body.

When I got to the hem of her skirt I brought both of my hands up her long moist legs and proceeded to pull her panties off. I thought I was hot before but by now I was boiling. Every fiber of my being wanted to just plunge into her release my seed into her belly and sleep for hours. But I knew I had to make her desire me for more of these trysts. So continued with steps one and two of Lily's instructions. After sliding her panties entirely off her body I nearly tore her feet off taking her shoes and socks off. She was wearing a loose pink ruffled skirt that seemed to make her look even more gorgeous. I wanted to leave it on her because it somehow made me even more turned on.

After stripping her of everything but the skirt I stood up and gave her a long steamy kiss. I felt her tongue probing at my lips and I opened them and was surprised with the ferocity with which Lily entered my mouth. I was starting to think she wanted this more then I did! The feeling of her tongue massaging my tongue drove me nuts and I returned the favor while at the same time lightly pinching her nipples. I took my lips away because I knew that if I didn't stop then I could kiss her for the rest of the day. I went back to her wish for me to lick all over her body. I licked up her nose and between her eyes. Across her forehead and down both cheeks. She was flushed and the red hue on her tanned skin was a sight that made me wish for a camera more then ever before. Not so I could remember, oh no. That sight is burned into my memory and will never escape. But so that others could see the beauty. I know that one look at her like this would make everyone forget their troubles. The fact that she was topless and wearing a short skirt would make them forget their names as well but it would still be worth it.

After I finished with her face I brought my tongue downward and swiped it over her chin before lowering to her neck. I made sure to not miss a spot with my tongue and when I got just behind her left ear she let out an erotic moan. I made a mental note of this spot. Somehow I must have missed her "zone." Years ago I discovered that every girl has a spot above their waste that turns them on immensely. When you find this spot and put just the right amount of attention there, the girl becomes putty in your hands.

I finished with her neck and started licking down her arms. Her perfect arms with just a hint of muscle. I sucked all of her fingers into my mouth and licked in the spots inbetween her fingers. After licking my way back up her body I stopped momentarily to glance at Lily's face. Her cheeks had become even redder and her eyes were closed. Her mouth was open and was biting her lower lip so hard I thought she would produce blood but she never did. I resumed my kissing and paid special notice to her shoulder blades. A lot of girls have a spot here that also turns them on. But Lily was not one of them so I quickly moved on. I brought my lips back to the spot on her neck and reveled in the sounds she made as I nipped at her skin.

Then I resumed my trek down her body. I had already explored her front with my tongue so I went down her back. I went down her body with the careful precision of a surgeon. No spot was left untouched. Eventually I found myself down at the skirt that attracted me so much. I kissed her body through the skirt and when I got to the end I just kept going downward. I explored every flaw in her body with extra consideration. If she had a scar I made sure to spend twice as much time on that part. Eventually I found myself at her foot. Now feet have always creeped me out. Not just the smell but the way they look. Lily wondered why I had stopped and looked down at me.

"You know I did say every part of my body."

I smiled up at her before bringing my face back down and kissing the top of her foot. Now she had been sweating a little because of her dancing but thankfully the taste was nowhere near as bad as I thought it would be. My fears nearly gone I resumed my licking and brought my mouth to her toes. What the hell, I thought. I already kissed every other part of her body. I brought one toe at a time into my mouth and sucked on them like I had sucked on her fingers. I heard Lily gasp above me and realized that she must have a foot fetish as well. After I put her third toe into my mouth Lily climaxed quite unexpectedly. It was the hardest I had heard her orgasm. I think this is the first time she realized how much she enjoyed having her feet played with. She would definitely force me to do this again. Well this is one more thing I can use to keep her coming back for more. Although admittedly I knew I would dread this part of the sex. But anything to keep the lady coming right? After finishing with the foot I licked back up her leg and repeated my ministrations on her other leg. I still hesitated a bit before kissing her foot but it was much less.

When I had finally gotten back to her midsection I was extremely relieved. My mouth felt chapped from all the kissing and my tongue was feeling quite sore. And I still had to eat her out! But at least this part I was ecstatic to do. Her skin tasted exquisite but her juice was the best thing I had ever tasted. I had only kissed her midsection through her skirt so I proceeded to finish step two. I started on her delectable derriere. She had just enough fat on it to make it round and bouncy. I had the strange urge to take a bite out of her ass but I resisted. After working my way back to her front I finished licking everywhere except where I really wanted to lick.

Lily's juices were dripping by now and she looked ready to burst. Even after her earlier climax she was in desperate need of release. I brought one finger to her leg and moved it up, capturing some of her juices on my fingers.

"MMMM! That is the best thing I have ever tasted. If you bottled this I would spend my entire paycheck to taste this."

I smeared some more on my lips to stop them from being so dry and then I finally brought my head down to the sweetest place on Earth. I thought briefly about going slow but knew Lily was close to orgasm and I was reminded of my ever-present erection throbbing inside my pants. Which I had somehow forgotten to take off during my Lickapalooza. I dove my tongue into Lily's sugary paradise and used every muscle my mouth had to bring her to a swift release. Lily's loud moans reminded me once again how lucky I am. That and the taste of Lily which is uniquely hers. A fact that infuriates me because I would love to discover something that remotely tastes like her but nothing else comes close. Remembering how she responded last time right when Lily was coming down from her post-coital high I stuck my finger into her asshole and was surprised at the looseness of it.

This brought Lily straight into another screaming orgasm. When she came back to earth I asked her why she was so much looser then last time. Granted she was still really tight but last time I could barely fit anything into her. Now my finger slipped in without too much of a struggle. Lily blushed before answering.

"Well I loved the feeling when you put your tongue and then your finger into my asshole last time. So for the past week I have experimented with other things going in there."

The image of Lily at home masturbating and putting things into her ass were too much for me. I needed to fuck and I needed to fuck now.

"Would you like something much larger put into your asshole? I am sure I could accommodate you."

Lily gleamed at me and nodded feverishly. I started undressing, loving the look of lust in her eyes. When I finally took my boxers off and my rock hard cock came out Lily gasped in shock.

"ITS…ITS…SO BIG! IT MUST HAVE GROWN 4 INCHES SINCE LAST WEEK! WHAT HAPPENED?"

I gave her some bullshit story about being sick last week and that I could not get fully erect when I am sick and she bought it. Got to love naïve girls.

"I don't think I can fit it in there."

I knew from my experience with Miley that I could definitely fit my cock in there. Miley was much tighter then Lily and Lily has an anal fetish. This would be easy.

"Don't worry. I will start with your pussy while at the same time prepping your asshole. You will be fine."

Lily seemed to accept that answer.

"So how should we do this?"

"Get on the floor on your knees. Here's a sweatshirt to put under your knees so you don't burn them on the carpet."

Lily got into position and I pulled the lube back out of my desk. After slathering my cock with enough lube and putting some on my fingers I got behind Lily in position. Lily was propped up with her forearms on the carpet and her head resting on the carpet. I think she was praying that it wouldn't hurt too bad. I raised her skirt up so I could see her lovely body and I could feel it. I slowly inserted myself into Lily's tight cavern. With my precum, the lube, and Lily's juices I went in easily. After about half of my dick went in I pulled back to her entrance and slowly reentered her. With one hand holding her hips so I could keep a rhythm I brought my other hand to her asshole and stuck a finger in. Judging by the intensity of Lily's moans she was enjoying it so far. I gave a hard thrust into Lily's cunt and at the same time forced another finger into her. Lily let out a mixture between a moan and a scream. I took that to be a good sign and went back to a slow pace of fucking her pussy and lubing her cunt. After a few minutes of this I entered a third finger into her asshole. My door had a mirror on it and I looked up to see a look of pure ecstasy on Lily's face. She was biting her lip to keep from screaming.

I took my fingers out of her asshole and pulled out of her pussy. I looped my arm around her and nestled my hand in her curls.

"This will only hurt for a while, and then it will be more pleasure then you ever imagined."

Lily nodded at my words and I started pushing my dick inside her. At the same time I fiddled with her clit so she would be distracted from the pain. After three slow thrusts I made it as far as my fingers had reached. I knew that whatever pain she had felt so far would exponentially intensify. To top it all off the feeling of her tight asshole plus the knowledge that I had just done this with her best friend was making me feel close to climax. I fought through these feelings and proceeded to anal fuck her. I was picking up speed now and the sounds Lily was making made it clear the pain had turned into pure pleasure. I was going just a little bit deeper with each thrust. Plus my fingers were still busy at work playing with her clit. Lily started moaning loudly now. She buried her head into the floor to remain quiet. I wasn't sure why she bothered. If anyone heard her when I sucked her feet they knew what we were doing. After another 10 minutes I had buried my entire dick in her and was mere seconds away from climax. I wanted to reach it at the same time as her so I shoved two fingers inside her pussy while still flicking her clit and leaned into her neck. I kissed that spot I discovered earlier and felt her release. The tight anal passage wrapped around my cock, mixed with how long I had been hard and sight of her face as I looked at her in the mirror triggered my orgasm and I just let it loose right into her asshole.

I fell off her asshole exhausted. I couldn't have gotten hard if Miley and Lily had 69'd right there in front of me.

"You weren't kidding. That was unlike anything I ever experienced before. That was even better then when you sucked my toes."

"Thanks, always here to help. Speaking of which do you want to repeat this performance sometime?"

Lily blushed, "Maybe. Just make sure you aren't sick."

We both got dressed and checked outside. There was no one in sight. We got lucky and no one heard our fucking. Apparently both Miley and Katie had went home. Lily whispered to me that she had left me a little present on my desk. When I went to check it out I found her stained underwear there. Means I had a memento to two great fucks. Wonder if I can think of a way to get them both later on?

As I was contemplating this the janitor walked in.

I hid the panties as fast as I could and hoped he hadn't seen them. "Hey Neil. What's going on?"

"Well apparently a lot of fucking! You didn't notice the video cameras we put up last Sunday didya?"

The color drained from my face as I turned where he was pointing. Sure enough there was a camera that had to have captured all of the action. "Is there anything I can do to keep this between us?"

Neil scratched his chin. "Well I can think of one thing. I noticed both girls left without underwear. Give me those and consider the matter forgotten."

"Both girls? I only have Lily's."

"Check the bed. You didn't bother to look very closely after you two had sex."

I was a little disappointed to lose my mementos but it was a small price to pay. I gathered both pairs of panties and handed them over. He then handed me 50 bucks.

"What's this for?"

"I was going to get a hooker tonight. But with the footage I have now I won't need one for weeks. In reality I owe you more!"

That brought a smile to my face and I sent him off. Not before he told me I was the lucking sumbitch to ever walk the Earth though. I sat back in my chair and thought about the last week. Neil sure hit the nail on the head there. I am damned lucky.


	6. Prom

Well it had been two months since cheerleading tryouts and I had kept up my "relationship" with both Lily and Miley without them finding out about the other one. Because Lily was on the team we were able to get together a lot more often without it looking suspicious. Miley was a rare treat that I got to enjoy but it worked out extremely well. Miley had so much pent-up sexual energy that when we finally got together for sex she was like a wild animal. It was an incredible arrangement. I got to have regular sex with Lily and hardcore raunchy occasional sex with Miley.

I had continued taking those sexual enhancement pills just so I could keep up with the two of them. Their sexual appetites seemed insatiable. Not that I am complaining at all. This is still the best thing that has ever happened in my life. I never would have dreamed of this kind of thing happening to me. I tried to pretend that it was just sex but I have to admit that I was developing severe feelings for the girls. I was feeling like an asshole for fucking one behind the other's back but I couldn't stop. It was like my conscience was being overpowered by my dick. I was still a little afraid of being caught and fired but both girls had gotten very good at alleviating my fears.

Then one day I walked into my house and was shocked at what awaited me. Miley and Lily were sitting on my couch with frowns etched into their faces.

'Shit, they finally found out. Wait, maybe not. Just play it cool.' "So what brings you two here? Do you have a question about something?"

Miley seemed to get madder at that. "Yes, we have a question. How long did you think you could keep fucking us both before we figured it out?" she nearly yelled.

Well by now I was really scared. I thought they might find out but I had no idea that they would be this mad. I thought Lily might be a little thrilled since she had showed interest in Miley. "I…um…didn't think it would be that big a deal."

"Well we'll show you how big a deal it is." They then both stood up and walked right up to me and got right in my face. And then they turned to each other and shared a long hungry kiss.

'Well I obviously died and went to heaven.' "Ummm….what….huh….god….hot." With that they finally broke their sexy kiss. Lily gave me her familiar slutty smile. "Well when we found out we were a little mad but then we started talking and certain…urges were brought out. We decided to use this experience to indulge in some of these urges. And since you were the one who brought out these urges we decided to wait until you could share with us this experience.

'Yep, I am definitely dead. If I had known heaven was going to be like this I would have killed myself a long time ago.' "You two are sure you're not mad? Not at all?" Miley leaned in and tried to inhale my lower lip. After a few seconds she pulled back and answered me. "Well we were very mad when we found out, and there are still a few feelings of resentment. So the deal is, we let you join in, but you have to be completely under our control." She pointed to the couch where some handcuffs and straps were located. "I had no idea you two could be so kinky. I like it. But how did you two find out about me having sex with both of you?"

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(Yesterday afternoon)  
Lily and Miley are relaxing at Miley's house. They had started talking about the upcoming prom. Miley seems a lot more enthusiastic then Lily. "I can't wait! Remember our deal about losing our virginity at the prom. We have to make sure to get suitable dates so we don't feel disgusted with ourselves the rest of our lives." "I can't take it anymore! I have to let you in on a little secret. I lost my virginity a long time ago. In fact almost a year ago." "Oh thank god. I didn't want you to know but I have been having incredible sex for the last couple months. I was just trying to keep up appearances. I am so glad I don't have to keep that in anymore."

Lily was shocked. She never would have dreamed innocent Miley would have any sexual experience. Let alone multiple times. "Really? Who have you been having sex with?" 'Shit! I forgot I originally had sex with him to get Lily that cheerleading spot. Well I hope she won't be too mad.' "Well I…sorta…have been fucking the Mr. Fineberg, cheerleading coach." 'Oh god I hope she doesn't hate me.'

'The cheerleading coach? Wait, so he is fucking both of us?' "That's who I have been having sex with too. What the hell! That bastard." "WHAT! Wait, why did you have sex with him?" "Ummm…Well I hate to tell you this but I knew I didn't have a shot at being a cheerleader unless I did some "extra tryouts" so when I went into his office I used my body to get the spot."

"NO! NO FUCKING WAY! After you told me how much being a cheerleader meant to you I went into his office and used my body to get you the spot. And to think you already had it. That bastard!" "You lost your virginity to help me out? Miley, you are the best." Lily leaned in and gave Miley a hug. Maybe it was the wonderful thing Miley did for her. Maybe it was all the talk about sex. Maybe she finally just couldn't hold back but Lily finally acted on her sexual impulses about Miley. Lily moved her mouth to Miley's mouth and kissed her. After a few seconds Lily backed up and covered her mouth with her hand. 'OMG! I can't believe I just did that. There goes the best friend I ever had!'

Miley was shocked that her best friend had feelings for her. But what shocked her even more was how good the kiss felt. It was the best kiss of her life. There was so much chemistry involved in that kiss that she stopped thinking and just acted. "OMG Miley I am so sorry aboGSH" Miley grabbed Lily by the neck with both hands and gave her a much more passionate kiss. After a few seconds Lily seemed to wake up and she started kissing her back. She pushed her tongue against Miley's lips which Miley quickly opened. Then the struggle for dominance began. Neither one seemed willing to submit and their tongues quickly tired with the effort both put into the kiss. Lily finally pinned Miley's tongue down and to celebrate she brought her hands up to feel Miley's breasts through her shirt.

That was when Miley broke the kiss. Lily worried she had came on to strong. "Wait, wait. I have an idea on how to make this even better." Lily looked at her questioningly until Miley filled her in on the plan. "Ooh, I can't wait. We get to enjoy some hot lesbian sex and get some payback on that bastard. Perfect." "Don't speak about him that way. Without him we never would have realized our feelings about each other." They kissed once more but quickly broke it off knowing they wouldn't be able to resist going further. Both girls then lay back in each other's arms and just enjoyed the feel of the other girl.

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(back to the house)

"It doesn't matter how we found out. Let's just enjoy each other's bodies for now. Now strip naked and get in the bedroom so the fun can begin." I had trouble remembering how to take off my clothes and ended up just ripping my shirt in two to get it off. Both girls were smiling at me as they grabbed the handcuffs and straps and followed me into the bedroom.

"We decided to wait until you could join us before having sex with each other so we are feeling really horny. I hope you don't mind if we go first." "Mind? No no no, don't mind at all. Just glad you two could get past your anger." I looked at them and waited for them to start. "Have you forgotten already?" Miley twirled the handcuffs in her hands and I remembered the deal. "Oh yeah, so where do you want me?" "Get on the bed you dirty boy!" With that kind of motivation I jumped right up there and got ready. My dick had been hard since their kiss so I was really anxious to get to the sex.

Lily and both took a side and handcuffed my arms to the bed-posts. Then they grabbed the straps and tied my legs to the posts at the end of the bed. "Umm, if I'm taking up the entire bed where are you two going to have sex?" "Why, right on top of you of course. Unless you have any objections?" My tongue was halfway down my throat by now but I managed to choke out a no.

They smiled at each other and leaned in to give another long emotional kiss. Both girls were extremely flushed when they finally broke it. Miley turned to me and gave me a sultry smile. "So do you like what you see so far?" "Uh-huh, uh-huh." "Well good, then why don't we try something to make it even hotter?" "That could be fun."

Lily pulled something out of her pocket and started walking over to me. Whatever it was she kept it behind her back and I couldn't tell what it was. When she finally got to me she leaned in and licked my neck. Then I jolted when I felt Miley stroking my cock. "Do you like that? Does Miley stroking you feel good? Are you ready to get involved?" "Yeah! Yeah! Of course!" Lily showed me what was in her hands and I nearly fainted. It was…a blindfold. "This is your punishment for corrupting two young innocent girls. We are going to be giving the show of a lifetime. And you won't be able to see it. If you don't complain too much we will still have sex on top of you though." Well to say I was infuriated would be an understatement but I was trapped. Better to at least be able to hear them and feel them then nothing at all. Plus if I pissed them off too badly they could just leave me here for God knows how long.

I tried to form mental pictures of what the girls were doing but it was impossible. I distinctly heard a zipper opening and a bra unsnapping. I could hear the sound of lips on skin but I had not idea where the kiss was or who was kissing who. "Oh Miley, suck on my tits! I have waited so long for this!" 'DAMN DAMN DAMN, best mental picture of my life and I know if I could see it would be the most beautiful thing I ever saw. DAMN!"

000000000000000000000000000000000000000000000000000000000000000000000000  
(Third-person point of view)

After blindfolding Mr. Fineberg the two girls seemed reluctant to start. To tell the truth they weren't too mad at Mr. Fineberg after realizing their feelings for each other. In fact they were quite happy and wanted to thank him. Plus having someone they had both already slept with would alleviate some of the tension from having sex with each other after years of friendship. But at the same time they didn't want him to get completely off the hook, especially since he had been screwing them both for months and they could have been having hot threesomes that whole time. So they definitely felt he deserved some torture, but actually having sex on top of him was too cruel. After a few seconds of waiting Lily suggested pretending for a while and then letting him join in.

Miley unzipped her jeans and pulled them down her legs along with her underwear. Lily took off her shirt and unsnapped her bra. Lily was about to ask what next when she felt Miley's tongue on her left tit and Miley's hand on her right. "Oh Miley, suck on my tits! I have waited so long for this!" Lily sunk down onto the bed and used one hand to hold Miley to her tit and the other to stroke her bare ass. One stroke went a little low and she felt Miley's wetness soaking her hand. Miley had by now changed places so her hand was on Lily's left tit and her mouth was lathering Lily's right. Using all of the willpower Lily had she pulled Miley away from her tits and frenched her for thirty seconds.

"If you keep this up it won't be pretending, I thought you wanted to include him in this?" Lily whispered. "I don't care about him, I have the idea of sex with you in my head and I saw you looking so radiant I needed you. We can always include him later." Lily knew if they kept going they would exhaust themselves and leave Mr. Fineberg high and dry. "You're spending the night at my place, we can do this then, right now we got a willing male that is going to explode from the mental pictures we must be giving him." Miley frowned but agreed to hold off.

That was when Lily realized that she had been lying on Mr. Fineberg's legs this whole time. And when she saw his throbbing cock she realized that saying he was about to explode was quite accurate. When Lily brushed his cock with her hand he groaned and raised his pelvis, searching for the contact. Miley walked to his face and took off the blindfold. "Have you learned your lesson?" Miley asked. Mr. Fineberg started nodding so fast he looked like a bobblehead. Miley gave him a sensual kiss, "Good, then we have one question for you. You look ready to cum, so who do you want to suck you off?"

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(Mr. Fineberg's point of view)

Now that question threw me off, I knew it wouldn't take long for me to cum with any type of stimulation. So a blowjob to finish me off was a good idea. But this question seemed dangerous. What if I picked the wrong one? So I went with the safe, and sexy, choice. "How about the both of you?" When they looked at each other uneasily I got scared that I screwed up, but the grins came back full force and they both climbed onto the bed, Lily straddling my left leg and Miley straddling my right. Lily was the first to bring her head in to lick the precum off. That right there almost got me and I had to control myself so I could get the most out of this experience. Next Miley brought her head down and started licking up and down my cock. When she went back up Lily came down and took the head in her mouth. She swirled the tongue around my dick and looked at me with her innocent expression that somehow is the sluttiest thing I have ever seen. This time Miley took the whole thing in her mouth and slowly bobbed her head a few times before letting Lily have her turn. Lily took the opposite approach and did a lot of fast bobs and that was when I felt Miley sucking on my balls and I exploded. Lily's mouth was filled to the brim before she pulled off and let Miley taste some of my semen. Lily pulled Miley into a kiss and it was the sexiest thing I have ever seen. Two beautiful near naked teenage girls with my cum on their faces making out near my cock. One last spurt of cum came out and landed on Lily's chest.

Eventually they pulled away from the kiss and started licking my cum off each other. When Lily was clean except for her chest she stopped Miley from licking it off. She got on her hands and knees and crawled up my body and presented her chest to me. "Come on, you know you want to." I was hesitant to taste my own cum but at the same time intrigued. Plus I was still horny as hell after that show and sucking on her tits would help somewhat. I couldn't move much so Lily had to smother me with her chest, not complaining in the least, for me to lick the cum off. While I was licking the beautiful chest of one Lily Truscott, Miley was not inactive. She had already gotten her shirt and bra off before I started licking. When I finally got around to sucking on Lily's nipples Miley was already pulling off Lily's skirt and thong. Lily basically collapsed onto me and squealed so I had a good idea of what Miley was doing after undressing Lily. I felt something wet drip onto my chest only a few seconds after Miley started eating out Lily. Looks like Lily had gotten pretty worked up too, because I can't think of a time when she came that fast.

Lily rolled off of me and started gasping. I could finally see Miley and the wetness between her legs was quite obvious. I tried moving over to her but forgot about being tied to the bed. "You girls can let me go now." A smile came over Miley's face. I had never seen her smile like that. There was competition for Lily's innocent look for the sluttiest thing I had ever seen. "Now why would we let you go? We told you this time, we call the shots." I was annoyed that I had to stay tied down, but couldn't help but notice she said this time. Meaning there will be repeat performances; this realization had the unfortunate side effect of making my dick twitch which did not go unnoticed by the sexy teens resting near me.

After a bit of giggling at my reaction the girls whispered while looking over at me and I couldn't help feeling like a piece of meat. It actually felt pretty good. All of a sudden they jumped into action and I was moaning at the velvety feeling of Miley's tight hole surrounding me. Miley gasped as she went down and paused, as if she was waiting for something. Then my view was blocked by the lower half of Lily. It appears Lily wanted this to be special because her hairs were shaved into a neat little triangle with the point aiming towards her wet pussy. Miley started rising and falling on my dick and I could hear slurping coming from Lily's other end and I realized what Miley had been waiting for. The image of what used to be sweet innocent Miley riding my dick while the never innocent Lily licked her clit was getting me very excited. Then I started feeling Lily's tongue on my cock as I moved in and out of Miley and it was like sensation overload. I couldn't move but I felt like I needed to do something. I moved my head as little as I could and my nose brushed up against Lily and I could hear her moans. I hadn't realized I would be able to pleasure Lily but the girls had given me just enough room. I buried my head into her muff and couldn't believe how wet she was. Miley started shrieking and I got the idea that Lily must have reacted to my tongue and responded in kind. Miley was thrusting herself harder now and I used what little movement I had to thrust up hard into Miley while nibbling Lily's clit and pushing my nose as far as possible into Lily. I was always made fun of for having a pointy nose but I thanked God for my honker now. Suddenly my nose was saturated with Lily's juices and her moans mixed with the sounds of flesh as Miley continued to bounce on me. Lily rolled off of me and I finally could watch Miley wantonly bounce like a whore in heat while she needed her small breasts with both hands. This sight pushed me over the edge and I came hard into Miley, taking her over the edge with me. Miley collapsed onto me, not even bothering to take my dick out of her, and passed out. I couldn't believe how tired I was considering I was barely able to move the whole time, but I followed her and Lily into sleep soon after.

Well 1 person has asked for lesbian sex, which would be the orgy I am planning on doing, or planning on skipping, still haven't decided. I want at least 1 more to ask for it before I try and write it. I will probably write one more threesome because I wish I had put more into this but I wanted it done by Christmas. Thanks to the one person who e-mailed me and asked me to continue. That, alongwith me losing power and having nothing better to do with my laptop battery, inspired me to finally finish this chapter. I started and stopped writing this a few times, I hope it isn't noticeable but it probably is. Thanks to everyone who has been reading this. I looked at my hits and I am over 10000! That is insane. And thanks to everyone who has reviewed, although I wish there were more of you. Hearing that people like my story is what makes me write. I hated leaving this unfinished since I knew there were people that wanted this. Sure it is 8 months behind schedule, but…well…I got it done eventually.


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